Iodoethane → 1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1H-indole

HRID 1767960ノート

反応式

HRID 1767960 の反応式
C([Li])(C)(C)C.[CH3:6][CH2:7][CH2:8][CH2:9][CH3:10].BrC1C2[C:15](=[CH:16][CH:17]=[C:18]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])C=2)[N:14]([Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH:13]=1.C(I)C>C1COCC1>[C:32]([Si:29]([CH3:31])([CH3:30])[N:14]1[C:15]2[C:7](=[CH:6][C:18]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[CH:17][CH:16]=2)[C:8]([CH2:9][CH3:10])=[CH:13]1)([CH3:35])([CH3:34])[CH3:33]

参加物

6

反応物 4

HCID 6340IodoethaneHCID 8003PentaneHCID 236144893-bromo-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indoleHCID 178418306HCID 178418306、化合物

生成物 1

HCID 236144791-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1H-indole収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A 1.5 M solution of tert-butyllithium in pentane (3.3 ml, 4.99 mmol) was added dropwise to a solution of 3-bromo-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole (1 g, 2.3 mmol) in THF (6 ml) at −78° C. under an argon atmosphere. After 15 min ethyl iodide (0.37 ml, 4.5 mmol) was added at −78° C. The reaction mixture was stirred for 30 min at −78° C. and for 2 h at RT. After quenching with saturated aqueous NaHCO3 solution the reaction mixture was partitioned between ether and water. The organic layer was dried over sodium sulfate and concentrated in vacuo to give 880 mg (2.26 mmol, 99%) 1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1H-indole.

後処理

  1. customAfter quenching with saturated aqueous NaHCO3 solution the reaction mixture
  2. customwas partitioned between ether and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-323d2ce04c7c4c7581fde6a0622321d6
出典データセット
uspto-grants-2007_06
特許番号
US07235572B2

反応ノート

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